


The One About Jack

by HolyFuckingHell



Series: Dean and Cas’s Time [2]
Category: Supernatural
Genre: Awkward Conversations, Awkwardness, Castiel/Dean Winchester First Kiss, Confessions, Emotional, Emotions, First Kiss, Fluff, M/M, Soulmates
Language: English
Status: Completed
Published: 2020-12-29
Updated: 2020-12-29
Packaged: 2021-03-11 04:08:39
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,655
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28409019
Author URL: https://archiveofourown.org/users/HolyFuckingHell/pseuds/HolyFuckingHell
Summary: Dean really did not like Jack at first. He has his reasons. It takes a while for Dean to come around but eventually he does. This is the story of how and why Dean warms up to him. And it's also the story about Dean and Cas's first kiss.
Relationships: Castiel & Dean Winchester, Castiel/Dean Winchester
Series: Dean and Cas’s Time [2]
Series URL: https://archiveofourown.org/series/2069001
Comments: 15
Kudos: 110





	The One About Jack

**Author's Note:**

> Ideal I would write smut for every fic I write but unfortunately for me, and maybe y'all, Cas and Dean took the beginning of their relationship pretty slow.

Dean really did  _ not _ like Jack. He didn’t even like him before he was born. For multiple reasons. 

Firstly, he’s the son of Lucifer. That’s not exactly a good start. But truthfully, Dean is learning, and he probably could have looked past that. Everyone gets to make their own choices, but not when it comes to your parents, he gets that. So blindly hating this newborn kid because of that, Dean now knows, is stupid. 

But! Something he can not and will not look past is the second reason, Jack took Cas away from him. They had some kind of father/ son bond? Something? It was weird and is weird and Dean still to this day doesn’t understand. He really can’t comprehend why Cas would leave him and hide from him and ditch him, passed out in the park. Cas wouldn’t do that, there’s no way. He had to be tricked or controlled or confused because his Cas would never do that. And the sheer thought that he would willingly do that to Dean-  _ And Sam. Both of them. Dean and Sam.  _ Dean can’t believe it. He refuses to even  _ think it.  _

And finally, the biggest reason Dean doesn’t like him is because now, Cas is gone. Jack’s here and Cas is gone. And Dean feels infinitely broken. Shattered across the universe. It’s Jack's fault. It has to be. If Jack wasn’t here, Cas would still be with him, alive and well. With him. 

But Cas isn’t. His best friend is gone. And now Sam and Dean are stuck with the child of  _ Satan.  _ It’s not fair, but then again, nothing ever is. 

Dean  _ really  _ does not like Jack. 

And yes, deep down, Dean knows that it wasn’t Jack who put the blade through Cas’s chest, but it’s so much easier to blame Jack for the whole situation. 

He’s not blaming Jack intentionally. It’s just his subconscious grieving for the loss of the best guy Dean’s ever known. And, god, it hurts so bad. 

Now every time he looks at Jack it feels like a reminder that Cas is gone. With a feeling like that, he finds it very hard to control the anger and resentment he shows toward the kid. 

Sam talks to him about it constantly. How he needs to give Jack a chance. Sam is really worried that Dean is gonna try to kill him. And yeah, Deans thought about it. It’s not that he  _ really _ wants to kill Jack, it’s just that he wants Jack gone. And the horrible feeling in his chest that he’s been ignoring too. He also wants that gone. They’re linked, he thinks. They have to be. 

But after a hunt with Jack, after Jack saves both their asses, Dean warms up a bit.  _ A bit.  _ Like moving something from the freezer to the refrigerator. And of course,  _ Sam _ wants to talk to Dean. 

Dean apologizes for being difficult. And unfortunately, Dean also gets pretty emotional to no fault of his own. And it’s embarrassing because it’s in front of Sam. 

He’s not balling, but there are tears in his eyes and a lump in his throat. “I just-” Dean chokes. “He’s gone and-” Dean closes his eyes and takes a deep breath. He doesn’t say anything else. 

“I know…” Sam says sadly. “It sucks.”

Dean just sniffles and nods. 

Sam knows how Cas’s death is affecting Dean. How it always affects Dean. He drinks constantly with literally  _ no care _ about his health. He’s grumpy and irritable. He sleeps a lot. This time feels much different than the other times though. 

He’s always a little worried about Dean. But now he’s  _ very  _ worried about Dean. He’s never seen him  _ this bad.  _ Bad? Yes. But Sam has never seen anything like this  _ at all.  _ As dumb as it sounds, he’s worried Dean may actually die from grief. Worried he’ll go to sleep and he just won’t wake up or something. He knows it’s medically possible for stressful life events to be fatal. And Dean is always so stressed anyway. Sam is concerned this might do it for him, like his heart might  _ literally  _ give up and go out. It seems frighteningly realistic. 

He tries not to think about it and hopes everything will turn out as okay as possible. 

But then not too long after that night, Sam and Dean run into a very much alive Cas at a phone booth. Sam was more than elated. But then he looked at Dean. Dean who is so happy and relieved and filled with joy and so many other  _ obvious  _ emotions that it looks like he’s about to cry again. And Cas looks just as happy to see Dean. Sam doesn’t say anything about how long their hug lingered. 

And from there, Dean’s whole demeanor changed. Towards everything, even Jack. 

If Sam had to describe it in one word, that word would be ‘bouncy.’ 

And then Dean finding out immediately after they get to go to the land of cowboys?  _ Super _ bouncy. 

Dean honestly  _ loved  _ dressing up like cowboys with his brother, his best friend (newly back front the dead again due to his stubbornness to come back,) and the half-angel-half-kid that is now somehow part of their makeshift little family. 

Dean asked Cas again, this time privately when they had more time, how he made it back and Dean is so obsessed with the way he did it that Dean can’t stop talking to Cas about it. 

“So you just  _ woke up.” _ Dean is laying on the bed at the motel and Cas is sitting at the foot of it, facing Dean. They just finished up the hunt in Tombstone but are staying the night at a motel, deciding to make the drive back tomorrow. Sam offered to go get them food and Jack went with him. Him and Jack get along pretty well and have that kind of relationship. 

“Yes,” Cas laughs. They have been over this a few times. 

“And you didn’t like… See anything?” 

“No,” Cas shakes his head. 

“Describe it again, I can’t picture it…” Dean asks, listening intently. 

“Well,” Cas starts, “There is really nothing to picture. It was an infinite void of nothingness.”

“Just like… Black? Was it black?”

“It was nothing.”

“Could you see?” 

“I could see the entity residing there when it allowed me to. And I could see myself. That is all.” Cas offers. 

“This sounds so fucking creepy, dude.”

Cas laughs a small bit, “It was not ideal…”

“That sounds like an understatement,” Dean smiles at Cas. “So you said you walked around so… you could move…”

“Yes, I could move.”

“Was there like… A floor? Were you walking on a floor?”

“Dean,” Cas laughs, “You are failing to understand what I mean by eternal nothingness.”

Dean chuckles, “I know, I’m sorry, it just seems so…” Dean can’t think of the right word. 

“Incomprehensible.”

“Yeah,” Dean agrees. “So then you talked to the thing and it looked like…  _ You?”  _

“My vessel, yes.”

“Weird. And it told you to sleep again? Because it wanted to sleep and it couldn’t do that unless you slept?”

“Yes.”

“So,” Dean starts laughing, “You refused to go back to sleep so it sent you back!”

“That is correct.”

“That’s my favorite part of the story!” Dean nudges Cas with his foot. Cas glances down as he does it and smiles. 

“Why?” Cas chuckles. 

“Because you got to come back! And the reason it let you is because you were being a stubborn jackass! It’s awesome!” They both laugh. “Here’s what I don’t understand-”

“What the empty looks and feels like?”

“Well yeah, but no. I don’t understand- The empty says no one wakes up, right?”

“Yes,” Cas nods. 

“So… How come you woke up?”

“Something… Called to me…” Cas straightens his face. 

“Right…” Dean nods. “Like… Like what?”

“I’m not sure,” Cas looks away in thought. 

Dean wonders if it was him. He prayed to Cas like crazy. And in a moment of weakness, even Chuck. He just wanted Cas back so bad, he would’ve done anything for that. 

“I’ve thought about this a lot actually,” Cas starts again, drawing Dean’s attention back to him. “It would have had to be something very powerful, like Chuck or Amara. But that did not make sense to me because I doubt they would care if I was alive or not. But if either of them did, they could have brought me back themselves.”

“So… What then?” Dean doesn’t think it was him. He’s not powerful, he’s a human. They are pretty low in the power pyramid. 

“I think… Maybe… It was Jack…” Cas says softly. 

“Jack?” Dean breaks. 

“It’s the only thing that I can make sense about.”

“Jack is the reason you’re back?” Dean swallows. 

“I believe he woke me up, yes.”

“Oh…” Dean doesn’t know why he feels bad now, but really,  _ he does know.  _

Sam and Jack walk in with pizza. It startles Dean. How did he not hear the car?

“Everything okay?” Sam asks, looking weirdly at Dean and Cas. 

“Uhh, yeah!” Dean sits up. “Tell me that’s pepperoni and we’ll be more than okay…”

“It’s pepperoni!” Jack smiles. 

Dean smiles back at Jack. “Perfect.”

They end up in the bunker later the next day a little bit before a normal dinner time. They all get settled back in. Dean takes a long-awaited, much needed,  _ long _ shower. It’s been a while since Dean has taken a  _ long _ shower if that  _ makes sense.  _ But today, he might as well. It’s been long enough and he’s feeling pretty good. And cleaning up is easier in the shower than in his room so he might as well. 

His shower is actually  _ very relaxing.  _ It was warm and soothing and he seriously feels refreshed. And in a good mood. 

He walks to his room, half dry, towel around his waist, hair all fluffed up in weird directions. He changes pretty leisurely. His good mood is making it pretty hard to find the clothes he wants to wear. They’re all good. 

He puts on a pair of jammie pants. He only has two because he almost  _ never _ wears them. One is all blue with white drawstrings, the other is black with old Cartoon Network characters all over it. Not a specific show, just the network. He decides on the all blue ones because they are softer. 

And that’s exactly how he picks the shirt he wears. He thinks it’s probably his softest one. It’s also a little big on him, but that part is kind of nice. It says “Pronounced Leh-nerd Skin-nerd” on the front. 

He stops by the kitchen to grab a beer before going to the library to find Sam. Halfway there he feels sort of bad that he didn’t grab Sam a beer but as he walks up he realizes Sam already has one. 

He also realizes that Jack is in there too! They seem to do a lot of stuff together. Dean sits next to Jack.

“Whatcha reading?” Dean asks Sam. 

“A Natural History of Monstrous Creatures… It’s pretty cool but I don’t know how accurate it is. But I guess that goes the same for all these books, right?” Sam answers, glancing up at Dean. 

“I guess that’s true…” Dean shrugs. He doesn’t really know. 

“What about you, kid? What are you reading?” He looks at Jack. 

Jack looks at him pleasantly surprised, “Uhm, an encyclopedia of rare monsters… It’s quite good! Sam suggested it to me!” 

“Nice,” Dean nods, drinking some of his beer, “What’s your favorite one?”

Jack looks pleased that Dean is showing interest in him and is excited to answer. He’s thinking.

“What do you mean his favorite?” Sam interjects. 

“Well,” Dean chuckles. “Obviously we don’t  _ like  _ any of them, but some are cooler than others you know?”

“‘Cooler?’” Sam judges. 

“You know what I mean… Like dragons… Don’t want one, obviously, but they’re cool!” 

“Dragons?” Sam laughs. 

“Well or like… Angels. They’re pretty cool. And rare. Or at least they used to be.”

“Angels?” Jack says. 

“Yeah, I mean, you know the kinda stuff they can do… It’s boss as hell! Even if most of them are total dicks.”

“I like…” Jack contemplates, “Sirens. They seem pretty interesting.” 

“I get that,” Dean nods.

“I guess sirens are pretty cool.” Sam gives in. “I see what you mean, but it still feels like… A weird question.” 

“Ehh, gotta appreciate little stuff though, right?” Dean drinks some more. 

Sam looks at him strangely, “Right…”

“Well,” Jack starts again, “Maybe fairies.”

“No!” Dean laughs,  _ remembering. _ “Not fairies…”

“What happened?” Jack asks curiously. 

“Story for another time, kid.”

“Alright,” Jack nods. 

Dean thinks it’s a little funny that he was able to walk in and distract everyone. “So uh, anyone know where Cas is?” Dean asks. 

“He is somewhere around the bunker,” Jack offers. “He was just here a few minutes before you came in.”

“Oh,” Dean nods. That reminds him. “Hey, uh, Jack?”

Jack turns to him. 

“I think I owe you some kinda apology. I was upset and angry and…” Dean swallows. “I wanted Cas back and felt helpless and I took it out on you and that wasn’t fair.” Dean looks away and drinks more of his beer. 

“It’s okay, Dean. You were grieving.”

“Well, no. It’s not okay. I shouldn’t have acted that way. I’m… I’m sorry.”

“I forgive you.” Jack smiles. 

Dean feels a little better. This kid just forgave him. And he seems to get it. Is Jack cool?

“Well,” Dean clears his throat, “Also, as far as I understand it, you’re… Kinda the reason Cas is back.”

“Cas is resilient and strong, Dean.” Jack closes his book finally. “I am sure he found his own way back to us.” 

“Maybe…” Dean nods, not dismissing the theory. Jack is right. Cas  _ is  _ resilient and strong. And smart and clever. He might be right. “But he seems to think you played a large part in it, so thank you…”

“If that’s true,” Jack shrugs, “There is no reason to thank me. I’m glad Castiel is back. I feel very strongly connected to him. I feel the same with Sam as well.” Sam kind of smiles. Dean nods. “And I think I am starting to feel it with you too!” 

Dean half-smiles. “Sorry it took me a minute to come around. You’re a pretty cool kid.”

“You’re a pretty cool adult!” Jack smiles. “I realize now that you were not yourself because your soulmate was gone.”

“Yeah,” Dean nods. He drinks some of his beer. Halfway through, he chokes for a second. “Wait, what?” Dean says quickly. 

“Castiel was gone,” Jack helps. 

“No, I got that part. Uhm,” Dean exasperates. “Soulmate? What the hell is that supposed to mean?”

“Oh!” Jack smiles. “A soulmate is a person ideally suited for another as a close friend or a romantic partner.”

“Oh,” Dean nods. He looks at Sam who is staring quietly and weirdly at him. “So like… Close friends, that’s what you mean…”

“Well, I guess you and Castiel  _ are _ close friends, but also romantic partners. That’s why the term works so well for you two. Because it’s so accurate!”

“Uhm,” Dean looks awkwardly at Jack, blushing profusely. “We aren’t ‘romantic partners.’”

“I’m sorry, Dean, but it seems very obvious that you are.”

Sam clears his throat, “Jack,” he grunts. Jack and Dean both look at him and watch as he shakes his head to signal Jack to stop.

“‘No’ what?” Jack asks. “No, they are not partners?”

“No as in stop talking…” Sam whispers seriously. 

“Wait, Sam, -What?” Dean looks confused and partly horrified. 

“Oh, are we not supposed to talk about it?” Jack tilts his head. 

“Wh- F- Thah!” Dean sputters. “There’s nothing to talk about!”

“I don’t understand,” Jack says confused. “You two are not together?” 

“No!” Dean laughs nervously. 

“But it’s clear you care for him very much. And he cares about you too…”

“Did he say that?” Dean asks. 

“No,” Jack shakes his head. “He didn’t have to, it’s excruciatingly obvious. Same with you! Right Sam?”

They both look at Sam. Sam stares blankly, seemingly upset that Jack just tossed the talking stick to him. He doesn’t say anything. 

“Sam, you don’t think Cas and I are together, right?” Dean asks after moments of awkward silence and staring. 

Lucky Sam, Dean kinda saved him. “No!” Sam breathes out deeply. “I know y’all aren’t together.”

“Why did you try to get Jack to stop?”

Well, so much for luck. “Uhm,” Sam chuckles awkwardly. “Maybe we should just drop this-”

“Sam,” Dean scolds. 

“Well, I told him to stop because uh…” Sam laughs again, still nervously. “We aren’t… Supposed to talk about it,” Sam grimaces. 

“What the fuck?”

“Dean… Think about it…” Sam looks away. 

Dean stares blankly. Thinking about it. “What? There’s noth- There’s nothing to think about…” 

“Okay…” Sam nods. 

“Dean,” Jack pipes up again. Dean looks at Jack, horrified again. “It’s okay.”

“What?” Dean stutters. 

Jack puts his hand on Dean’s shoulder. “It’s okay that you and Cas have feelings for each other.”

“But I- I don’t have-” Dean swallows. “I don’t have feelings for Cas…”

Jack looks sadly at Dean and drops his hand. “I guess the reason we aren’t supposed to bring it up is because you haven’t acknowledged it… I understand now, sorry.” 

Dean is breathing very hard.  _ “‘We?’  _ Who is we? Sam?” Dean looks to Sam. Sam looks away. “Oh fuck,” Dean pants.  _ “OH FUCK.” _ No one says anything as Dean just processes. He crosses his arms over his chest. “You think-!” Dean looks at Sam. “And you think…” Dean looks at Jack. “Do I…” Dean pants. “Do I have feelings for Cas?” Dean asks, horrified still. 

“Yes,” Jack smiles. 

Dean looks at Sam. 

“Yeah…” Sam whispers with a nod.

“Oh fuck.” Dean closes his eyes and drinks the whole rest of his beer. “No fucking way,” Dean pants. “What do I do?” Dean asks. No one understands what he means so no one says anything. “Damnit, Sam! Why did you never tell me?!” Dean pants, upset. 

“I thought you were ignoring it!” Sam explains.

“I didn’t know!”

“We thought you knew!”

“UGH! What do I do now?” Dean asks again. 

“What do you want to do?” Jack asks Dean. 

What  _ does  _ Dean want to do? He’s been hit with all of this new information at once and he is confused. And terrified. And now Dean is overwhelmed and thinking too much.  _ “Son of a bitch!”  _ Dean shouts. 

“What’s wrong?” Cas asks, stepping into the room. Everyone turns and stares at Cas silently. Cas tilts his head, confused. “Are you all well?” Sam and Jack look at Dean. 

“Cas,” Dean stands up. 

“Yes?” Cas asks, confused. 

Dean walks swiftly towards Cas, cupping his face with both hands and pressing their lips together. They wind up with Dean pressing Cas softly into the wall. 

“Jack,” Sam says, sounding shocked. “The kitchen! We uh, we need to- Let’s go to the kitchen!” 

Cas is obviously shocked at first but then leans into him, wrapping his hands around Dean’s forearms. 

It feels really weird for Cas. He didn’t think this would ever happen. But it feels really nice, his lips are so soft. Cas gets  _ very _ excited. He doesn’t know what’s going to happen, but he knows it’s going to be good. 

It feels really weird for Dean, too.  _ Really weird.  _ He’s kissing a dude. And he  _ likes it.  _ Not just any dude, he’s kissing Cas. And he can feel Cas’s scruff against his a little and  _ that’s new.  _ But it also kinda feels nice. Like he’s been waiting for this to happen for a while… A long while. How long has Dean liked Cas and not known it? 

Dean moves his body closer to Cas so they are pressed together. Cas is actually surprisingly good at this. His lips are so warm and- Holy fuck, that’s his tongue. Cas is using tongue. And it feels amazing. But then he pulls away so Dean steps back. 

“Dean,” Cas gazes at his eyes. “I don’t understand what- What is happening?”

Dean pants. “Jack, he- He told me…” Dean bites his lip and nervously flattens his hair back and down. “Damnit, Cas…” Dean’s eyes start to fill with happy-tears and he tries to force them away. “I missed you so damn much!” Dean hugs Cas very abrasively, probably the most abrasive hug Cas has ever received, and swallows. “You came back,” Dean’s voice breaks, “Thank you, Cas, so much for coming back to me…” 

“Dean,” Cas says softly. “Do you want us to be together?” Cas says cautiously. His voice brakes too, “I’m so confused…”

“Yeah…” Dean squeezes Cas closer into him. 

“Let’s be together… I’d like that…” 

“Good,” Dean grunts, still holding Cas tightly to him.

“Okay,” Cas closes his eyes and relaxes his body into Dean. “Uhm, Dean?” Cas pipes up after a few calm, still, peaceful moments. 

“Yeah?” Dean says softly. 

“I like your pajamas. They are very soft.” 

Dean laughs and sniffs, “Thanks, Cas…”

Dean is  _ forever  _ grateful for Jack. He saved Sam! And he wouldn’t be with Cas if Jack hadn’t have done what he did. He woke Cas up, he brought Cas back, he… Embarrassed Dean a whole ass bunch but he needed to and he’s glad he did. He owes Jack so much. Ugh! Dean would legally adopt him if he could. 

It’s good that Jack is in their lives. Dean only wishes he knew that from the start. He still really doesn’t forgive himself for how he acted in the beginning but Jack keeps insisting on forgiving him. If Jack can forgive him, Dean knows he should be able to forgive himself. And he really tries. 

He’s a great kid. Dean doesn’t understand  _ how  _ he ended up that way, but he is. For multiple reasons. 

**Author's Note:**

> There will be smut next time, swear!
> 
> Comment what you think!! Please!! I'm beginning! I love y'alls comments!!
> 
> Also, email me if you have any ideas for them! I'm always open and looking! And if anyone is interested in proofreading a fic or two for me, let me know. I'm super dyslexic and these errors are getting out of hand. You would get to read them before I publish them! If that's at all enticing! 
> 
> Email me! watsondude00@gmail.com


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